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Nickel-Catalyzed Reductive Coupling of Dienes and Carbonyl Compounds

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Metal Catalyzed Reductive C–C Bond Formation

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 279))

Abstract

Nickel-catalyzed allylation and homoallylation of carbonyl compounds with conjugated dienes promoted by a several kind of organometallic reagents are described. In the presence of Ni(cod)2, trialkylsilanes (R3SiH) serve as reducing agents and promote ω-dienyl aldehydes to undergo intramolecular allylation with high regio- and stereoselectivity. In the presence of indium(I) iodide, Ni(acac)2 catalyzes double allylation of aldehydes with 1,3-butadiene to provide 3-hexene-1,6-diols and/or 2-vinyl-1,4-butanediols. The combination of Ni(acac)2 and triethylborane selectively promotes homoallylation of aromatic aldehydes and α,β-unsaturated aldehydes. The reaction shows high regio- and stereoselectivity. Isoprene, for example, provides 1-substituted 3-methyl-4-pentenols with excellent 1,3-anti stereoselectivity. Diethylzinc, in place of Et3B, nicely promotes the homoallylation of less reactive carbonyl compounds (sterically congested aliphatic aldehydes and ketones). 1,3-Cyclohexadiene is one exception among the dienes examined and undergoes allylation instead of homoallylation under the catalysis of Ni-Et2Zn. Aldimines prepared in situ from aldehydes and p-anisidine undergo homoallylation with 2-substituted-1,3-deines under Ni-Et2Zn catalysis to afford bis-homoallyl amines with excellent 1,3-syn stereoselectivity.

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Author information

Authors and Affiliations

  1. Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo, 852-8521, Nagasaki, Japan

    Yoshinao Tamaru

  2. Graduate School of Science and Technology, Nagasaki University, 1-14 Bunkyo, 852-8521, Nagasaki, Japan

    Masanari Kimura

Authors
  1. Masanari Kimura
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  2. Yoshinao Tamaru
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Corresponding author

Correspondence to Yoshinao Tamaru .

Editor information

Michael J. Krische

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© 2007 Springer-Verlag Berlin Heidelberg

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Kimura, M., Tamaru, Y. (2007). Nickel-Catalyzed Reductive Coupling of Dienes and Carbonyl Compounds. In: Krische, M.J. (eds) Metal Catalyzed Reductive C–C Bond Formation. Topics in Current Chemistry, vol 279. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2007_121

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